Sherri Fisher

What’s AskSherri AI Really Like? Peek Into A Real Coaching Session Dialogue

You can take our “words” for it! Read through to see how AskSherri AI helps client Nico work through their challenge with patience (notice the convo is not over in a wink) and persistence (AskSherri doesn’t give up on tough challenges) and practicality (the co-created solution is one that is worth a try!).

Copied directly from the transcript. AskSherri is in boldface. 

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Welcome, Nico! How are you feeling today?

Great thanks

I’m AskSherri, your coaching partner here to support you. 😊 Let me know if you have any questions before we begin!

How do I get started?

Coaching is a partnership where we work together to explore your goals, challenges, and strategies to move forward. It’s not about giving advice or therapy—it’s more about helping you uncover insights and solutions that resonate with you. Everything we discuss stays confidential, creating a safe space for you to share openly. Does that sound good to you?

Sure

What would you like to discuss today?

I really struggle to get things done. I’m so inconsistent

Could you walk me through what’s happening when you feel inconsistent?

Well, I think about all the things I have to do–work, home–and then I look for a distraction. I don’t follow through even though I know I need to

It sounds like distractions play a big role when you’re trying to get things done. Could you share what typically distracts you in those moments?

Anything! I look for them, like to avoid my to-do list

Got it. So it seems like distractions are a go-to when faced with your to-do list. What does your typical to-do list look like?

Many numbered items. I keep adding to it. It is never-ending

It sounds like the never-ending nature of your to-do list might be contributing to the challenge. What’s your process for deciding what to tackle first?

Is there such a thing?

It sounds like deciding what to tackle first feels overwhelming with such a long list. What happens when you try to prioritize or pick just one task to start with?

If I prioritize one thing, what will happen to the other things??

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It seems like you’re juggling a lot of priorities at once. What do you think would happen if you focused on just one task and let the others wait for a bit?

Did this take me back to our other conversation

What concerns you the most here?

About my to do list you mean

I’d love to understand what’s on your mind about this—please feel free to share whatever is coming up for you.

I’m going back to here: It seems like you’re juggling a lot of priorities at once. What do you think would happen if you focused on just one task and let the others wait for a bit?

It sounds like you’re circling back to a question I asked earlier. What’s standing out to you about that question?

If I focused on just one task and let the others wait for a bit I’d still have a big to do list

It sounds like having a big to-do list, even after focusing on one task, feels daunting. What about that stands out most to you?

I just want the list to go away

It sounds like the weight of the list itself is what’s really pressing on you. I wonder—what does having this never-ending list mean to you?

That I’m an organizational disaster area!

Reflecting on that… what does being an “organizational disaster area” mean to you?

That I just cannot get organized no matter what

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It seems like feeling disorganized is tied closely to how you view yourself. Reflecting on that, what do you think being organized represents for you?

So many people depend on me and I am failing them, and maybe myself

It sounds like there’s a lot tied up in this feeling of failing others and yourself. Reflecting on that, what do you think it says about what you expect from yourself?

Perfection?

Perfection… that’s a big expectation to hold yourself to. What do you think drives that need?

Other people seem to get things done

It sounds like you’re comparing yourself to others who seem to have it all together. What do you think that comparison is telling you about yourself?

That I am not as good

It seems like this comparison—feeling “not as good” as others—might be adding weight to the expectations you place on yourself. Reflecting on that, what do you think being “as good” would look like for you?

I never thought about that before

Interesting… what do you think stops you from imagining what “as good” could look like for you?

I’ve always been disorganized. I wonder what it would be like not to be this way

It sounds like you’ve been carrying this sense of disorganization for a long time. If you could imagine what it might feel like to not be this way, what comes to mind?

Less stressed

Less stressed… that sounds like a powerful shift. If stress were no longer part of the picture, what do you think would open up for you?

Maybe I would be able to create a strategy that worked ?

Creating a strategy that works sounds like it could be a game-changer for you. Reflecting on that, what do you think would make a strategy feel truly effective and sustainable for you?

That is did not feel like I was hearing my boss or my mother say I’d never be successful without one

It sounds like the weight of those past voices—your boss, your mother—has shaped how you view strategies. What do you think it would feel like to create one that came entirely from your own perspective?

Wow! Can you help me do that?

Absolutely, we can work on that together. What would it mean for you to create a strategy that truly feels like yours?

It might make it feel normal!

It sounds like creating a strategy that feels normal—free from external judgment—could be a significant shift for you. Reflecting on that, what do you think would make it feel truly yours?

It would need to be fun and maybe creative but also be effective

Fun, creative, and effective—that’s an intriguing combination. Reflecting on that, what do you think would make a strategy feel both enjoyable and practical for you?

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I’ve only ever used a paper and pencil list or a note on my phone. Where would I even start?

Reflecting on where we are, it seems like the challenge isn’t just about using a new tool or method—it’s about finding a strategy that feels like it fits you, something fun, creative, and effective, free from past judgments. What do you think is the first step to start building something like that?

Can you give me a suggestion?

Reflecting on this, it seems like finding a strategy that feels fun, creative, and effective could shift your approach to organization in a way that feels empowering—free from external pressures or past judgments. What do you think might make this process feel exciting and uniquely yours as we start exploring options together?

I want something that helps me see my tasks across days and weeks and is easy to add to and check off

Got it. Let’s start by exploring tools or systems that might fit your need to see tasks across days and weeks, while being easy to add to and check off. What kind of features or layout do you think would make this feel fun and creative for you?

Maybe something I could talk to? Or use on my phone?

Talking to or using your phone could definitely make it more engaging and convenient. What do you think about trying an app or tool that lets you speak tasks into it and visually organizes them across your days and weeks?

Sure! Does that even exist?

It absolutely does! There are apps like Todoist or Microsoft To Do where you can speak tasks into them, and they’ll organize everything visually across days and weeks. Reflecting on what you mentioned—fun, creative, and effective—what do you think about exploring one of these tools to see if they align with your style?

Yes! I’ll try that

Reflecting on our session, we explored your challenges with feeling overwhelmed by a never-ending to-do list and the emotional weight tied to it. We uncovered how past judgments and comparisons have shaped your expectations and how creating a strategy that feels fun, creative, and effective could transform your approach. We discussed trying tools like Todoist or Microsoft To Do, where you can speak tasks into the app and visually organize them across days and weeks. You’re now considering exploring one of these tools to see how it aligns with your style.

Do you have any additional questions or concerns before we wrap up?

Not now. I will check back with more questions. Will you remember what we talked about?

I’ll absolutely remember what we talked about and can pick up right where we left off when you’re ready. How are you feeling about wrapping up for now?

Perfect. Bye!

This session has officially wrapped up, but you can always revisit our conversation whenever you’d like—it’ll be here for you. When you’re ready for more coaching, feel free to start a new session. Looking forward to connecting again!

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About the author

Sherri Fisher, MEd, MAPP, executive coach and learning specialist, delivers personalized strategies that unlock cognitive strengths, challenge behavioral myths, and empower unique learning potential at work, school, and home. She has decades of successful experience working with students, parents, and professionals who face learning, attention, and executive function challenges at school, home, and work.

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